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Novel diphenylethylene compounds

A technology of compounds and compositions, applied in the field of new stilbene compounds, can solve problems such as unknown genetic factors

Inactive Publication Date: 2002-06-19
CALYX THERAPEUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Insulin secretion and insulin resistance are considered major defects, however, the exact genetic factors involved in pathogenesis are still unknown

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of 2-(4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)-sodium acrylate

[0032] To a mixture of 3,5-dimethoxybenzaldehyde (30 mM) and p-hydroxyphenylacetic acid (30 mM) was added 5 mL of acetic anhydride and 2.5 mL of triethylamine (TEA). After stirring at 130-140°C for 24 hours, the mixture was cooled to room temperature, and the reaction was terminated with 25 mL of concentrated hydrochloric acid, and CH 2 Cl 2 extraction. The organic extract was further extracted with 1N NaOH, then the NaOH extract was washed with water, the aqueous layer was acidified with conc. HCl, and washed with water to give the crude product. Acid I was obtained by recrystallization of the crude product from ethanol / water.

[0033] To obtain 1 g of decarboxylated I, 3 g of copper powder and 30 mL of quinoline were stirred and refluxed for 4 h under nitrogen. The reaction mixture was filtered, diluted with water and washed with CH 2 Cl 2 extraction. The organic layer was dried and co...

Embodiment 2

[0036] General procedure for the preparation of styrene derivatives

[0037] General procedure: To a stirred solution of Wittig's salt (1 mM) in anhydrous THF at -78°C was added potassium (bistrimethylsilyl)amide (1 mM). N 2 After stirring at -78°C for 2 hours under atmosphere, HMPA (2 mM) and aldehyde (1 mM) in THF were added and stirred at room temperature for 16 hours. The reaction was quenched with water and extracted with diethyl ether. The product was purified by flash chromatography.

Embodiment 3

[0039]Referring to Fig. 1, STZ-induced diabetic rats were obtained by intravenous injection of streptozotocin (STZ) (40 mg / kg / body weight). Blood glucose levels were measured 72 hours after STZ injection. Rats exhibiting a fasting blood glucose level greater than 200 mg / dl were used for the experiment. The compound of Example 1 was orally administered to test rats at a dose of 20 mg / kg / body weight. At the same time, the control group was given vehicle PBS (phosphate-buffered saline). Glucose tolerance test was performed shortly after administration: glucose (2g / kg / body weight) was administered, and blood glucose levels were monitored at different time points. The results are shown in Figure 1. Between 30 and 60 minutes after dosing, the blood glucose levels of the rats administered the test compound started to decrease.

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Abstract

Novel diphenylethylene and styrenes are provided which are administered orally to decrease blood glucose levels in rats. The glucose tolerance in insulin resistant rats is also shown, as well as lowering of triglyceride levels in serum insulin resistant, hyperinsulienmic and hypertriglycedmic rats. The compounds are orally effective anti-diabetic agents that potentially may reduce abnormality of glucose and lipid metabolism in diabetes.

Description

field of invention [0001] The present invention relates to novel stilbene compounds and their use in the treatment of diabetes. Background of the invention [0002] Extracts of the leaves, flowers, and gums of the rosewood tree (Pterocarpus marsupium Roxb.) (Fabaceae), also known as the Indian chino tree, have been traditionally used in the treatment of diarrhea, toothache, fever, and urinary tract and skin infections . Extracts from the bark have long been considered useful in the treatment of diabetes. Manickam et al. reported in J.Nat.Prod., 1997, 60:609-610 that the naturally occurring pterostilbene isolated from the heartwood of Pterostilbene, namely trans-1-(3,5-dimethoxyphenyl) - Hypoglycemic activity of 2-(4-hydroxyphenyl)-ethylene. However, this pterostilbene is water insoluble and has not been shown to be effective in treating diabetes, especially in the presence but inactive insulin. The cause of diabetes is unclear, although both genetic and environmental fac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P3/10A61K31/05A61K31/085A61K31/09A61K31/192C07C39/15C07C39/19C07C39/205C07C43/215C07C43/23C07C59/68
CPCC07C43/215A61K31/192C07C59/68A61K31/05C07C39/15A61K31/09A61P3/00A61P3/10A61P5/00C07C15/50
Inventor B·纳格S·麦迪彻拉D·戴
Owner CALYX THERAPEUTICS
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